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Macrocyclic Effects in the Mesomorphic Properties of Liquid-Crystalline Pillar[5]- and Pillar[6]arenes
Auteur(s)
Nierengarten, Iwona
Holler, Michel
Karmazin-Brelot, Lydia
Barbera, Joaquin
Nierengarten, Jean-Francois
Date de parution
2013
In
Eur. J. Org. Chem.
Vol.
18
No
2013
De la page
3675
A la page
3684
Résumé
Whereas the reaction of 1,4-bis(2-bromoethyloxy)benzene (4) with paraformaldehyde in the presence of BF3·Et2O afforded exclusively the cyclopentameric pillar[5]arene deriv. (5), both cyclopenta- and cyclohexameric macrocycles 5 and 6 were obtained when the reaction of 4 with paraformaldehyde was performed at 45 °C in CHCl3 with FeCl3 as the catalyst. Treatment of compds. 4-6 with sodium azide provided the corresponding polyazides, to which a cyanobiphenyl building block was subsequently grafted to generate model compd. 1, pillar[5]arene 2, and pillar[6]arene 3, bearing two, ten and twelve mesomorphic subunits, resp. The liq.-cryst. and thermal properties of the compds. were investigated by polarized optical microscopy (POM), differential scanning calorimetry (DSC), and X-ray diffraction (XRD). Comparison of the liq.-cryst. properties of macrocycles 2 and 3 with those of 1 revealed the strong influence of the macrocyclic pillar[n]arene core on the mesomorphic properties. Whereas only a monotropic mesophase was obsd. for 1, a broad enantiotropic mesophase was evidenced for both pillar[n]arene derivs. [on SciFinder(R)]
Identifiants
Type de publication
journal article
